Tuscan base - Radda? Or San Gimignano Or Castellina or Montepulciano... so many to choose from

Radda is lovely as is Relais Vignole. We have also stayed in Castellina several times , also Panzano. Perfect bases. Montrpulciano takes you farther south but is a wonderful town too. I would never stay in Sam Gimiginano as it is tour bus central all day long.

What villages/towns do you plan to visit in your 2/3 days with a rental car ?

Frances Lodge is a great B&B overlooking Siena where one can walk into town, yet have the countryside feel.
Borgo Argenina is awesome outside of Castellina where Elena cooks with her guests and the breakfasts overlooking the winery are sublime !
We plan to visit Cretaiole on our next visit. Isabella is a fabulous host but this property is further south.

And some agriturismos may want a week lodging and you only have 2 nights.

Look at a map and see if Radda is within an hour to an hour and a half drive. Radda may be a great base for you.

I looked at Relais Vignale and Spa on Google maps. It's in a wonderful location, just outside the city walls of Radda. Radda is a lovely little town in a beautiful region.

Sadly, two nights means one day, which isn't nearly enough time. You could easily spend all morning in Radda. That leaves little time for anything else. I suggest scooting to Castellina for the afternoon.

Ciao,

Montepulciano is by far, one of my favorite towns in Tuscany. It's quaint, but not too small, has wonderful shopping, and some of the best restaurants I have ever dined at. I tend to travel there multiple times per year and it never disappoints. Using Montepulciano as a homebase for a few days allows you to explore the surrounding wine country and numerous other towns and villages.

If you decide this is on your list of places to stay, let me know and I would be happy to share restaurant and accommodation suggestions.

Have a fantastic trip! -TJ

I would love to hear restaurant recommendations as we are staying outside Montepulciano for four nights! Trip is getting close. Thanks to all for these great recommendations!

How wonderful! I hope you enjoy Montepulciano as much as I do. Here are my top dining suggestions:

L'Altro Cantuccio (http://www.laltrocantuccio.it/) – this is an amazing restaurant that puts a modern twist on typical local recipes. Their food is art, but it is not pretentious at all! This is a laid-back place that happens to produce amazing food.

Pane, Vino, & Zucchero – Again, another place that is in town, but more off the beaten path. Fantastic food and a hipper atmosphere – another place you can’t go wrong.

La Grotta (http://www.lagrottamontepulciano.it/intro.php) – this is probably the most elegant restaurant. It’s located at the base of San Biagio, the 500-year-old church at the base of town. While the first two restaurant are more laid back, this is a restaurant you should dress up to eat at. Wonderful food and wonderful service.

Pulcino's – This is a family run restaurant just outside of town. Everyone at the restaurant is related, so when I say family run, it’s family run! This restaurant is popular with tour busses, but that should not deter you – they have easy access from the main road. This is the most typical/local type restaurant.

Have an awesome time!

I put these in my folder and now WE have to return soon !

Thanks to everyone for their great suggestions!
We pick the car up outside of Florence at 8:30am and we were hoping to visit Greve, get gelato in Castellina and see Sam Gimignano on the first day. Spend the evening in radda perhaps.
Early the next morning head to sienna and then onto Montepulciano.
The 3rd day we will drop the car in chiusi and head to Rome
The restaurants sound great. Thank you for these recommendations!
I’ll keep having a think about where to stay 🤔

All of your ideas are actually doable. Chianti and Val D'orcia are very different and worth their own stays.: We always stay in Greve (partly because we are now friends with the owner of our favorite agriturismo) or Castellina (nice place there that also has a cooking school) and Montalcino (or nearby). Radda always seems a little out of the way (from 222), but it's quite worth a visit.